Most exit conversations start too late, skip the hard questions, and fall apart not because of the numbers — but because of the humans.
Brenda Jacobsen has watched this happen from every angle. She ran a corporate mindfulness media company through a merger and exit. She’s been the CFO who said no to deals that would have left the business insolvent. And now she’s a Managing Director at STS Capital Partners — a firm that, by design, puts former operators in the lead role on sell-side mandates, not bankers.
Her argument: the person who’s been through the emotional journey of decoupling from something they built is the right person to sit across the table from founders going through it for the first time.
We sat down with Brenda for one of the most practical and human conversations we’ve had on this show about what it actually takes to prepare for an exit. Here’s the full breakdown.
The Question Nobody Asks First
Before Brenda looks at a single financial statement, she asks one question: what are you trying to accomplish?
Not “what do you think the business is worth.” Not “when do you want to close.” What do you actually want your life to look like after this?
If a founder can’t answer that on the spot, they probably aren’t ready. And that’s fine — Brenda has invested years in relationships before a client ever signed an engagement letter. The readiness conversation is the beginning of the process, not a qualifier to skip.
When the answer starts to come out — more time with family, a cause they want to fund, a passion they’ve been deferring for fifteen years — something shifts in the room. Brenda describes it as a lightness, an energetic change. That’s when she knows the conversation is real.
The Owner’s Outcome Exercise
Brenda uses a two-page document called the Owner’s Outcome Exercise. It’s the most practically useful framework in this entire conversation and it applies whether you’re thinking about selling in six months or six years.
The exercise separates required outcomes from preferred outcomes. Required: the minimum financial number, key employees who must transition, buyer categories you won’t sell to, geographic commitments. Preferred: transition length, brand retention, location, culture preservation.
Here’s the critical part: Brenda asks each partner to fill it out separately and send it directly to her. She lines them up side by side, identifies the categories of strong alignment and the categories of divergence, and then brings everyone together to work through the gaps.
The document does three things:
It surfaces misalignment before it becomes a deal killer. Most misalignment isn’t malicious — it’s just never been discussed. One partner has been watching industry comps. Another has a personal debt load that’s been quietly shaping their number. A third hasn’t been involved in operations for years and has no idea what the business is actually worth. These are solvable problems when you find them early. They’re catastrophic when they surface at the offer stage.
It anchors emotional decision-making. When a seller gets cold feet at the offer stage — which happens constantly — Brenda pulls out the document. “This is what we agreed to. We’ve hit every required outcome. We’ve also hit two of your preferred outcomes.” You cannot force someone to close, but you can give them a rational framework to counter the emotional voice telling them to walk away.
It creates a documented record. Promises made in verbal conversations between partners evaporate under deal pressure. The exercise makes it real, signed, and referenceable.
Run Your Business As If You Could Sell It Tomorrow
Brenda’s prescription for exit readiness isn’t a checklist you complete in the six months before going to market. It’s an operating posture you maintain from day one.
What does “sellable tomorrow” actually mean?
You’re not the hero. Someone else can manage the key client relationships. Someone else can close deals. The business can operate without you in a way that’s demonstrable to a buyer.
Cash is not starved. Buyers read cash-thin businesses as high-risk. They use it to push down enterprise value. Keep the business funded.
Client concentration is managed. No single client should represent more than 20% of revenue. Brenda has personally felt the burn of a top client declining and the margin compression that follows. Buyers price this risk in aggressively.
Growth is real and documented. Selling a future story requires showing traction toward that story. If your pitch is “we’re going to 3x in three years,” a buyer needs evidence you can execute against a plan. Historical growth is the only credible foundation for forward projections.
Revenue is committed. Retainer-based models outperform project-based models in buyer eyes. Multi-year contracts are better than single-year. Contractual engagement removes execution risk from the buyer’s underwriting.
The AI Conversation Every Seller Is Having Wrong
Ayelet’s line from the top of the episode deserves to be repeated: stop BS-ing your AI story.
Buyers are now asking about AI in every single deal. Most sellers are either overclaiming (”we’re an AI-powered agency”) or underclaiming (”we use some AI tools”). Neither is helpful.
What buyers actually want to see:
Real efficiency gains. Are your margins better because AI has reduced the human hours required to deliver work? Show that. Revenue per employee trending up is a concrete metric that signals AI is working.
Pricing defense. If competitive pricing pressure is rising and you’ve maintained margins by integrating AI, that’s a value story. Tell it explicitly.
Proprietary data. This is the most underappreciated one. Who owns the data created by your work product? Brenda cited a current deal in outsourced radiology where the imaging data — patient demographics, diagnostic codes, billing history, community health patterns — is worth more as an aggregated data asset than as a component of the operating company. If your business generates valuable data as a byproduct of service delivery, understand what you own and whether you’ve documented the rights.
A credible AI roadmap. Even if you haven’t executed on it yet, a documented plan for how AI will improve the business is a legitimate part of the value conversation. Buyers with operational capabilities can underwrite unrealized potential if the thesis is coherent.
What gets you dismissed: mentioning AI in the first paragraph of your CIM with nothing to substantiate it. Buyers have been burned enough to tune this out immediately.
What the Market Looks Like Right Now
Current EBITDA multiples for digital marketing agencies: 3-6x is the safe range to plan around. Premiums are available for the right combination of growth, client diversity, recurring revenue, and strategic fit with the right buyer.
Dry powder is still significant. The cost of capital has risen, which compresses PE multiples modestly. But strategic buyers aren’t constrained by debt markets the same way. Which is another reason Brenda focuses there.
The One Thing to Do Tomorrow
What’s the one thing a founder who hasn’t had this conversation yet should do tomorrow?
Start with yourself. Before you bring your partners into the room, answer the questions privately. Know what’s important to you. Know what you need financially. Know what you can live with and what you can’t. Then invite your partners to do the same.
The exit conversation goes better when it starts with clarity rather than negotiation. And it starts with you.
Brenda Jacobsen is a Managing Director at STS Capital, a global M&A advisory firm focused on selling to strategics. She has held the CEO seat three times across healthcare, media, and services businesses.
Subscribe to In/Organic for weekly M&A coverage across agency, SaaS, and lower middle market deals.
